Brett Cassis: The Music Man

by Charles McGuigan 05.2026

Almost two decades ago, Shanan Chambers opened what was destined from its inception to become one of the most popular restaurants on the Northside, called, appropriately enough, Northside Grille. Shanan found the property on Bellevue back in 2006, but it would take well over a year for the restaurant to open. Along with the city dragging its heels on inspections, the building itself was an absolute mess. Shanan’s father came in from Seattle to help with the renovations, and Craig Nattoon, a master carpenter, lent his expertise to the project. Shanan’s dad built the massive rectangular bar, which seats more than 25 people, in the dead center of the restaurant. It’s flanked on either side by a total of 16 ample booths.

From the beginning there was a harmony between the front of the house and the back of the house along with consistency, both in food and service. They navigated the uncertain waters of recessions and a pandemic. On about the time that Northside Grille was coping with Covid, a man with a background in both food service and the booking of bands joined the team. And it was this man, Brett Cassis, who did something extraordinary with the full support of Shanan and the tireless efforts of the entire staff of Northside Grille. He brought music back to the Northside in a major way.

Over the past couple years, my son Charles and I have attended scores of performances by musical artists, along with meals and drinks, at Northside Grille, and we were never even vaguely disappointed.

We know all the servers and the managers and the bartenders, even the kitchen staff, along with all the regulars and many of the newcomers, and it’s really more like being at home, surrounded by extended family. And then there are the musicians we have come to know, the men and women Brett Cassis books for the shows—folks like Brady Heck’s Holy Roller, Ramona and the Holy Smokes, The Ex-Patriots, Mackenzie Roark, Brandon Wayne and His Lonesome Drifters (including the music dynamo and long-time friend known as Charles Arthur), Carmen Senski, Mike Lucas, Crack Fox, Prabir Mehta, and one of my favorite human beings on the planet, the gem of a lifetime—Susan Greenbaum. And like the staff, these creatives have joined the ranks of our cousinry, each with their distinctive styles and artistic quirks.

There’s a constant stream of talent performing at Northside Grille, Wednesdays through Sundays, either in the dining room or out on The Patio. They cover the entire musical spectrum, from classic country to trans-genres that might be a little metal flavored with neo-punk, and everything in between, all thanks to the know-how of Brett Cassis. 

Brett grew up outside of DC up in Cloverly, Maryland and he remembers driving around with his father and listening to Roger Miller and Johnny Cash on the car radio. “I guess Johnny Cash was my first introduction to music,” Brett says. His stepmother played Dylan and Neil Diamond albums on the stereo. “And then I kind of got into The Beatles for a little bit, and then it all kind of evolved,” he says. “When you’re young, you have a different personality from year to year.”

And then in high school the brother of a friend of his introduced Brett to another band. “It was The J. Geils Band,” he recalls. “Everybody else was into Lynyrd Skynyrd and (Led) Zeppelin. But for me it was J. Geils.”

His exposure to music then mushroomed. After school he would retreat to his bedroom, hours before his parents arrived home from work, clip on his headphones and listen to the radio phenomena WHFS—the first FM station in the DC market to broadcast in stereo. He’d listen attentively to one of its DJs, Weasel (Jonathan Gilbert), who possessed an encyclopedic knowledge of every conceivable kind of music and would often interview some of the greatest artists of the era. Brett fell in love with George Clinton’s Parliament Funkadelic. “And punk was just starting up, so I followed that, too,” he says. “With Weasel you could hear Jerry Lee Lewis at one point and then an entire funk album. Weasel was all over the map.”

And so was Brett. “I caught a lot of flak from people in high school because I liked Elvis Costello or  Iggy Pop and glam rock,” he remembers. “I liked it all.”

In his high school years, Brett had a fair amount of spending money because of different after school and weekend jobs he worked at a sub shop or a mini-golf course.  And with that wad of cash he would make his way on Saturdays over to Kemp Miller Records or Waxy Maxies and piss it all away on vinyl albums.

After high school, Brett headed south to Richmond where he planned to attend VCU and study graphic arts. He got a job at a Friendly’s on West Broad Street and by the age of 19 was assistant manager. For a time he thought he’d work his way up to manager. He was a quick study and had learned a lot about the food industry from the ground up. But he had a change of heart, and decided to go back to school and study art.

At about that time, Brett was working with a rugby friend name Billy Caudle and they were sanding the giant dance floor of Bird in Hand, a pawnshop in Shockoe Bottom that was transformed into a three story restaurant and nightclub.  “I ended up getting a job there picking up beer bottles,” he says. But he would also go on to work there as an assistant manager for a short stint.

That’s where he met two men who would change the course of his life. “They were Chuck Wrenn and Rocco Yates,” says Brett. “And I became a disciple of both of them.” Chuck was a bartender there, but also DJed and booked the bands. “I then picked up DJing and then I was helping Chuck with the bands,” Britt tells me.

After leaving Bird in Hand, Brett began booking bands at different clubs around town. “I would build relationships with different bands and club owners,” he says. He would also end up booking bands at The Flood Zone.

Back in the mid-nineties, Brett worked side by side with Dan-O Deckelman in putting together Route One South, a three-night music festival loosely patterned on South By Southwest (SXSW). It featured more than 300 bands performing at some 30 venues in and around Richmond. Along with a host of volunteers, Brett and Dan-O brought musicians from up and down the East Coast—New York to Florida—to play in Richmond. It lasted for two years.

“And then I went to work for Lee Johnson at Main Stage Productions,” says Britt.  “I helped over there, booking gigs and doing some management. Lee’s a great guy.” Brett would assemble the portable sound stages that were introduced while he was working there. “We were one of the first markets to have those stages,” he says. “I was blown away by how they put it together and how quickly it went up.” This is the same kind of stage Lee has donated in years past to the merchants of Bellevue Avenue for their annual Christmas on MacArthur. (Lee happens to be good friends with Jimmy Tsamouras.)

“Those stages are the industry standard now,” Brett explains. “So, I was at Main Stage for eleven years. I left there and tried to focus more on my family because I was often away on the weekends.”

He tried for awhile selling memberships to a sort of Costco competitor that never really took off. And then he moved to Charlottesville and commuted to DC for work with a stage company there. All the while he was also managing restaurants in Charlottesville. He ultimately moved up to Washington where he would live for the next six years before returning to Richmond. Things were tough, and Brett pieced things together the best he could.

“I was always working a second job,” he says. “I had to juggle two or three things, but I didn’t bitch about it. I can remember working at one point from eighty to a hundred hours a week.”

Back in Richmond, he worked at Chewy’s and HomeGoods, found an apartment on MacArthur Avenue, and shortly before Covid struck, he applied for a job at Northside Grille. “I left my name and number, but never heard back,” he says. But as soon as Northside Grille reopened after the pandemic, he went to work there, initially waiting tables.

“It was great,” says Brett. “The neighborhood was great. Our customers were very generous. We were jamming constantly.” He wanted to get behind the bar, but there were no open shifts. “That's when I started booking the music,” he says. “That was in 2022, I think.” For a short time he also served as a manager. Finally, though, he worked solely on booking bands and getting everything just right for the artists. A couple years in, they added a sound system, and the acoustics improved astronomically.

Like a baseball field in an Iowan cornfield, Northside Grille as a music venue drew forth the players—musicians all. And they just keep coming.

Since the first show held there, more than 300 bands have played at Northside. Every week, according to Brett, four or five new bands contact him to book a gig. And though many of the bands are local, the word has gotten out. This past March The Dra-culas played to a full house.  And on August 28, two-time Grammy winners Los Texmaniacs will play the patio, which can seat about a hundred. Though there is still no cover charge for the bands in-house (there are tip jars and make sure to fill them, musicians need to eat, too), tickets are required for The Patio concerts. And with bands like Los Texmaniacs it’s a good idea to purchase your tickets early. To reserve tickets you can visit thenorthsidegrille.com

The success of Northside’s premier music venue is definitely collaborative. “When people say, ‘You do an amazing job with this,” says Brett, “I tell them, ‘No, it’s everybody who works here, and it’s the bands.’ We treat the bands well. We make sure we feed them. We make sure they make enough money.”

He lavishes praise on the staff, everyone from the back of the house to the front of the house. How seamlessly things run from an organized kitchen to a host of diligent servers, and an impeccable bar that keeps the libations flowing.

Brett then mentions the woman who manages the front of the house. “Casey (Wade) was able to bring in people that had worked in the business,” he says. “She’s great and so is Dan in the kitchen.”

And then Brett Cassis says this: “It’s not just the staff, it’s not just the bands; it’s the customers and the neighborhood.  It’s the owner, Shanan Chambers. This is why it all works.”